New alkaloids from Stemona tuberosa and structural revision of tuberostemonols P and R.
Fitoterapia
; 176: 105998, 2024 Jul.
Article
em En
| MEDLINE
| ID: mdl-38734212
ABSTRACT
Three Stemona alkaloids named stemotuberines A-C (1-3) with unique C17N frameworks, presumably formed by elimination of the C-11-C-15 lactone ring of the stichoneurine skeleton, were isolated from the roots of Stemona tuberosa. Their structures were elucidated by spectroscopic analysis, X-ray diffraction, and computational methods. Compounds 2 and 3 showed inhibition (IC50 values of 37.1 and 23.2 µM, respectively) against LPS-induced nitric oxide production in RAW 264.7 cells. In addition, concern was expressed about the reported plant origin (S. sessilifolia) of the recently described alkaloids tuberostemonols O-R (4-7), which should be S. tuberosa. NMR calculations indicated structural misassignment of these compounds except for 6. Isolation of tuberostemonol P (5) from our material of S. tuberosa allowed for a close examination of the spectroscopic data leading to the revised structure 5a. Tuberostemonol R (7) was found to have identical 1H and 13C NMR data to the well-known alkaloid croomine, and therefore its structure including relative stereochemistry must be revised as 7a.
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Texto completo:
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Base de dados:
MEDLINE
Assunto principal:
Raízes de Plantas
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Stemonaceae
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Alcaloides
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Compostos Fitoquímicos
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Óxido Nítrico
Limite:
Animals
Idioma:
En
Revista:
Fitoterapia
Ano de publicação:
2024
Tipo de documento:
Article